Rudy Wins The Grand Prize

by the Troubador

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Heterosexual, Humor, .

Desc: Sex Story: A love story. Average joe wins sales contest and gets a trip to the Caribean. There things go cockeyed.

Reaching carefully from his stool at the bar, Rudy pulled the Hawaiian Sunrise up in front of him, stirring it gently with the little green umbrella. Holding the glass up to the sun he squinted through the bright colors now disbursing from the layers into which they had been poured. He tried to remember how many kinds of rum were there but gave up. Blearily staring at the collection of bar glasses in front of him, he wondered who the joker was that had been putting their empty glasses down in front of where he was sitting.

"Damn nasty thing to do" he thought. "The place was short handed, and the bartender seemed to have only enough time to make new drinks for the crowd, not to pick up the empties." Counting slowly he made it up to four empty glasses before losing count. Hiccuping, he almost fell off the stool. "Lucky," he thought to himself, "almost dropped my drink in the pool."

Swaying a little on the tall barstool, he cursed the wind that must be blowing to make him so unsteady when all he was doing was sitting quietly at the bar. He didn't want to stumble off the stool, placed as it was out in the center of the swimming pool. He had swum over here for a drink, but was dry now and figured he would walk back on the stepping stones that led to the patio from the bar.

Looking down at his baggy, tropical print bathing shorts he was amazed to see how dry they were. In the states he would have expected it to take several hours to dry so completely. Amazing how fast things dried down here in the tropical sun.

"Well, guess I'll go back to my cabana and take a nap before dinner," he mumbled. Easing slowly off the barstool Rudy drained the Hawaiian Sunrise then left the glass on the bar with all the others. Carefully stepping from stone to stone he made his way toward the edge of the pool. "Good Golly, Miss Molly," he thought, "these things must be floating to move around like this."

He was maneuvered to the next to last stepping stone when he began majestically swaying, pushing his arms out to the side where he slowly rotated them in large circles trying to balance. Onlookers later teased him that he had looked like ancient movie footage of the infamous Tacoma Narrows Bridge collapse, and nicknamed him Galloping Rudy. He twisted and turned, his movements becoming more and more uncoordinated before somehow managing to turn his arms one way, his body another and his knees an impossible third. Finally, seeming in slow motion, he toppled into the water, thinking as he fell, "Sure glad I didn't spill that drink!"

A minute later, the lifeguard fished him sputtering from the pool, and sent him on to his cabana with an attendant to make sure he got there all right.

Rudy was three days into the trip of a lifetime. His company had announced a sales contest for that summer. The Grand Prize, which nobody had ever won, was a two-week stay for two at a Caribbean Island Resort. It happened that was the summer everything Rudy had learned about his company, its products, and salesmanship suddenly came together.

Rudy had once been described as almost an average man. He wasn't quite tall, wasn't really athletic, but you couldn't say he wasn't tall or athletic. He just seemed to be kind of almost average. His sandy hair always seemed to be slightly disheveled, and though he had a nice wardrobe, his clothes seemed to be just a trifle mussed. Everyone was taken with his happy grin, which almost never left his face, and the girls all seemed taken by his twinkling eyes. He worked hard, but until the sales contest his supervisor's best description of the job he did was just about average. That was why Rudy was so excited about winning the Grand Prize.

Overnight Rudy found it was so much fun selling he wanted to do it 24/7. To his later astonishment that was almost what he did, for Rudy being single and unattached had no obligations at home. Clocking the greatest summer sales period the 100-year-old company had ever known Rudy won the Grand Prize.

Which gave him a problem. He not only didn't have a wife, Rudy didn't even have a steady girl. Certainly none of the girls he dated would even consider spending two weeks with him on a tropical island. For that matter there were none that he would consider asking to join him on a tropical island for two weeks. Actually, he never mentioned the trip to any of the girls he knew, being pretty shy. And he would be damned if he'd go off for two weeks on a tropical island with another guy. Although a couple buddies on his softball team hinted that it sounded like fun before saying, when he looked at them strangely, "Not that way, of course."

The problem was solved to his satisfaction when he talked the company into sending him alone for four weeks instead of him and a friend for two. He was proud of the salesmanship he used to talk them into losing their newly explosive salesman for a whole month. The clincher was pointing out that they would save hundreds of dollars on airfare if they only sent one person instead of the two they had budgeted for. The Vice President that had booked the trip at company rates didn't fight it too hard, he just took his secretary to Cancun again that year.

Rudy reached his island paradise Saturday afternoon, having left Friday afternoon and traveling the 'feeder line express' until climbing aboard the final leg on a flight out of Miami that morning.

Rudy had checked in, and begun checking out the ladies. Not surprisingly, all the women he saw were very firmly attached to men who were looking very proprietary. There were some real babes, along with some really nice looking older women he considered to be wives. He didn't know if the babes were wives or not and he sure wasn't going to ask.

Tired as he was, he didn't want to wait a moment to begin this dream. That was why he found himself falling into his cabana, a nice little bungalow a hundred yards from the main resort, and then crawling into bed. It was something he sure wasn't going to tell anyone about back home. That is, that he had been so bombed he fell through the door into his cabana and then had to crawl across the room and into bed.

Waking up the next morning he found fruit and juices had been delivered to his cabana before he awoke. It was a pleasant surprise to discover that whatever combination of fruits he had tried absolutely eliminated his hangover. Somehow he was never able to produce those results again.

He spent that day sightseeing and snorkeling. It was his first time in a snorkel mask, and it was even more fun than softball.

That evening Rudy enjoyed an elegant dinner and discovered the pool bar. It was stuck way out in the swimming pool, and it was obvious to Rudy only a wimp wouldn't swim out to get a drink. That evening he concentrated on Singapore Slings. Getting pleasantly mellow, he had a great conversation with some visiting Italians and went to bed after watching the sun fall into the sea.

Which led up to today. Rudy went snorkeling again that morning with a party from the resort. While in the water he met a party of Brits who had just arrived and were staying together in a large private bungalow about a mile down from his cabana. They all had a ball swimming, and the Brits joined him that afternoon at the pool bar. There they were joined by a quartet of nurses who also had just arrived from the states. When the Brits and nurses left to get dressed and ready for dinner Rudy had stayed for a few more drinks. That was when he began his experiment with the Hawaiian Sunrises and discovered other people were putting their empty glasses on the bar.

Rudy woke up in his cabana several hours later. He was still flying a little but anxious to get back to the resort for dinner. The Brits and nurses both had promised to be there for dinner and dancing. Rudy was darned sure looking forward to it.

The Grand Prize was looking like a real winner. Tonight was what two weeks in the Caribbean was all about. He was having a great time and to top it all off, he was going to be there an extra two weeks! Being honest with himself he didn't anticipate a bed partner. He was a pretty ordinary guy, and while the nurses were all great gals, good pals, they obviously wouldn't be into one-night stands. The Brits' women were all gorgeous but they were also very married and their men were there with them. The men were as big as their wives were gorgeous. Even more disgusting, they were nice people. "It didn't matter how great a salesman he was," Rudy told himself pedantically, "I couldn't do that to those nice people."

And that's how the evening went, up to a point. Sometime that night everything got cloudy. He remembered dancing a lot with one of the wives whose husband didn't like to dance. And he danced with the nurses. That memory black out cursed him the next morning.

Rudy awoke with a hangover. As he tried to focus his eyes on the ceiling it wouldn't stop moving long enough for him to accomplish the task. He rolled over to his left and almost fell off the bed in the process.

"This day is not getting off to a good start," he muttered to himself.

Rolling back onto his back, his right arm landed on something soft hiding under the covers. Looking over he saw blonde hair poking out from under the covers, then heard a sleepy moan coming from somewhere in that direction. The lump moved slightly and he felt a bare foot press against him as the movement stopped.

Maybe today wasn't going to be so bad after all!

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Story tagged with:
Ma/Fa / Consensual / Romantic / Heterosexual / Humor /